


Threesome

by fridarules, naniquena



Category: Supernatural
Genre: Anal, Anal Sex, Blow Jobs, Double Oral Penetration, Double Penetration in Two Holes, Drinking, Explicit Sexual Content, F/M, Friends With Benefits, Friends to Lovers, Fuckbuddies, Gay Sex, Happy Ending, Lingerie, M/M, Matchmaker anna, Minor Anna Milton/Dean Winchester, Multi, Porn With Plot, Porn with Feelings, Sexual Fantasy, Sexual Tension, Smut, Staring, Switching, They just have sex and don't care who bottom and who top, This fic has a translation to spanish, Threesome, Threesome - F/M/M, Vaginal Fingering
Language: English
Status: Completed
Published: 2015-09-12
Updated: 2015-09-12
Packaged: 2018-04-20 08:13:12
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 9,616
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4780178
Author URL: https://archiveofourown.org/users/fridarules/pseuds/fridarules, https://archiveofourown.org/users/naniquena/pseuds/naniquena
Summary: <blockquote class="userstuff">
              <p>Anna is a party girl with a plan in mind.<br/>Dean and Castiel are oblivious of their staring.<br/>Benny and Jo just wanna have fun.<br/>A bet and alcohol set a date.<br/>Will Anna succeed?</p>
            </blockquote>





	Threesome

**Author's Note:**

  * Translation into Español available: [Threesome -Versión en Español-](https://archiveofourown.org/works/4671098) by [DestielHispano](https://archiveofourown.org/users/DestielHispano/pseuds/DestielHispano), [fridarules](https://archiveofourown.org/users/fridarules/pseuds/fridarules), [naniquena](https://archiveofourown.org/users/naniquena/pseuds/naniquena)



She is a party girl. Her closest group of friends is quite eclectic; there’s an openly gay guy, a gay in the closet, a little sister, a womanizer guy and herself; whether she can be described as openly sex lover or plain sex addict, is your choice.  

Even though none of them is a teenager sex is always part of their group chats, but when she meets them separately- well, who am I kiddin’? They talk about sex as well. With Dean, on the other hand, she does way more than talking; they’re fuck buddies. They’re friends with benefits, the kind of friend you run to when you’re on a drought or you need to lose some steam. She shags him and it’s awesome.

The rest of the group is pure fun; Benny is openly gay and the funniest drunk ever, Jo is the youngest of the group and some sort of a sister to Dean, and then the fifth member of the group: Castiel.

Castiel is as shy as he can get when in presence of people, even when the group gathers he’s mostly quiet but laughs at the other’s jokes and drinks as much as any of them. Don’t get me wrong, he’s part of the group and loves these crazy bastards- he’s just shy. Only when it’s only the two of them going out, he opens up and he’s acts like someone utterly different. The reason though, not even he knows.

Now, you can consider her a sex addict but she is also a very observant person. What does she notice?, You may ask, nice that you bring it up. She’s been noticing that Dean and Cas like each other. How she found out is easy. Cas always flushes red when Dean’s name comes up in the conversation- like every time, and Dean is always trying to make her bring Castiel along when they hang out.

She is aware they both date girls; Dean is an amazing lover and Castiel may be shy but his eyes pop out when a nice ass goes by in front of him. But then again, every time they are in the same room they practically eye fuck each other.

Something has to be done.

Bold as she is, of course her best idea comes hand in hand with her kinkiest fantasy; so why not? She’s been thinking about this for weeks now, so it’s time. It came to a point where she would meet them and then back home she would need a -ehem- shower.

Thursday night the gang meet at their regular bar, beer on everybody’s hand –several beers, actually; they’re at that point where they’re loosen up enough to let themselves go and talk shamelessly about stuff– and sex.

Once they’re tipsy enough she sets her plan in motion.

“I wanna play a game”.

The rest of the table throw napkins at her and make boo noises, they know what kind of games she likes. Of course they’re just putting up a scene, they love her games.

“Yeah, yeah; you’re all cowards, I get it, bitches. Now, my game: I dare you all to drink two tequila shots in a row, the last one to drink has to tell a secret, but not any secret; it has to be a fantasy, the kinkier the better”

The bartender knows already their games so when they ask for shots he just leaves the bottle on the table and ask them to keep it easy; he knows how really loud they can be. In case you’re wondering the answer is very.

Jo does the honors. She’s decided she’ll become a barwoman, so she serves the shots and sits waiting for the order to ‘go!’; Every one of the five friends eyes the rest like measuring each other. They’re so freaking ready. When she shouts “GO!” they all gulp the first shot and with burning throats, they shove the second one in. They should have realized there was something going on- after all, when was the last time Castiel was a faster drinker than her- or than any of them, for the matter?

So she is the one to drink last. She lost. Did she? Ha!

Maybe it is because they’re all pretty drunk already, maybe it’s because it is the first time she loses a drinking game; the fact is that they tease her and laugh at her.

“Well, girl, your darkest fantasy comes first- shoot!” Dean leans on the table grinning and winking at Cas for no reason, just because.

Jo laughs hard and points at her, “Ha, Sister! When did you come so clumsy? Spill it NOW! Haha”

Benny doesn’t say anything, he’s not so drunk not to understand that she’s up to something, but for the sake of whatever her plan is, he stays put, smiling.

Cas won’t say a word, he’s never been the comfortable-talking-about-sex kind of guy. But he enjoys ‘everybody’s’ company, so he just waits to see where this is going. And he’s not eye-drinking from the greenest eyes on the table- no, Sir; if you’d torture him he’d forever deny it

“Okay, okay. Let me see-“ She pretends to think.

Four pairs of eyes are on her, expectant. Whatever she’s gonna say it will be incredible for sure.

“Don’t bullshit us!” Jo and Dean say at unison, making Castiel laugh a bit too hard.

“Have I ever? No, don’t answer that. Okay, ready or not. My biggest fantasy is having a threesome with two of the people on this very table” she pucks the table for emphasis, “I won’t give names, though; but you can make a guess” she whispers, looking at each one in turn.

Jo starts laughing, she can imagine at least one of the names her friend wants to shag- she does it regularly, anyway. Also she knows she’s out of the picture, because she isn’t into girls, not really. Now, the third name of the ‘some’ she can’t decide, either Benny or Cas would do. She’ll have to wait and see.

Benny looks at her, she winks at him; the guy lowers his gaze and takes his phone, whatever plan she has, she can count on him; he texts her.

«I’m in. If you’re up to what I’m thinking I’m in, and if I’m right about your plan, I think it’s time that they fuck each other into oblivion»

Cas would very much like to vanish in thin air, gazing at the table, doodling into the spilt beer, from time to time quickly glancing on Dean’s direction.

While all of the above was happening, Dean grew into the implication of her fantasy, “ANNA ELIZABETH MILTON—“, his tone scandalized, Anna’s look questioning, “Don’t look at me like that! You know what!”

“No, I don’t. Seriously, tell us, please” Anna manages to say without cracking into laughter.

Dean blushes furiously red, Cas thinks he looks cute; “I will never sleep with Jo, not in a million years, she’s like a sister to me, for Christ sake!” Dean is certain he’s one of the sides of the triangle but he can’t imagine whether the third one is a guy or… shit.

“Oh, no, darling, me neither. I don’t do girls and you know it. Ask Charlie; I’ve broken her heart more times than I can remember; not that it makes her stop, anyway”

Anna’s phone vibrates and she answers Benny’s text, «Maybe, if I manage them both naked in the same room they may lose the eye fucking. Help me out with this»

Meanwhile Cas, lost in his thoughts, finally comes to peace with the fact that a threesome with a girl and a guy has always been in the back of his mind; now his friends are talking about Dean being involved in one of those with Anna and another guy on the table. Shit. Cas’ brain is running a thousand miles per second, snapshots of him on top of the green eyed guy and, subsequently trying not to get hard and failing miserably. Fuck.

“Uhg” Dean grunts, finally understanding the implications of Jo being out of the picture. It all narrows to Benny, the gay guy, and Castiel, the guy he secretly has a crush on. A crush that it’s killing him because he’s straight and has never dug guys; only his dick obviously thinks otherwise, the fucker twitches every time Castiel is around.

The table’s gone silent, so, after reading Anna’s text, Benny speaks up, “It’s an awesome idea, if you’d ask me” he looks at Jo smiling and winks, “Jo and I can be the witnesses of this pact to fulfill Anna’s fantasy” None of the men implicated in the pact say anything- Anna supposes that makes it official, Benny continues “Let’s set the date. I say next Saturday at Seven; my advice is to have dinner and then- well, just focus on her fantasy. That’s it. I’ve just made the invites. You’re welcome girl.” Jo can’t stop giggling.

“Well, thanks Benny. But they still have to say ‘Yes’.” She takes turns to watch at Dean and Castiel; and the guys who have expressly avoided to look at each other after it was clear it was the two of them the ones involved in the task finally exchange looks Dean would never back off from a challenge, least if it involves sex. Dean challenges Cas, his chin raised and a smirk on the lips, in contrast with Castiel’s numb look, dead of embarrassment.

“I’m in” Dean says, looking straight into Cas soul, I mean, eyes. So everybody turns to Castiel, who’s red as a tomato.

“I don’t know- maybe” Cas whispers.

“What? Speak up, man!” Benny pushes.

“I said- maybe. Now stop staring, it’s creepy” Cas says a little bit louder.

Benny claps his hands, Jo looks at them open mouthed. Anna is practically drooling, Dean smiles coy and Cas just shrinks a bit- maybe that would help to conceal his hard on.

“Good, it’s a date then” Benny finishes and pours a new double round of tequila, “Now get ready because I wanna know someone else’s fantasies and I won’t lose”

Everybody laughs, but Cas can’t stop thinking of what he has agreed to. What the hell was he thinking? He has only two days to get used to the idea and get fucking ready. Oh gosh, he’s too anxious to think or function properly but he has to focus, because there is no way he’s gonna lose a round and have to share one of his own fantasies- all of them involving one member of the threesome team, and it ain’t Anna.  

The night ends after Jo and Benny tell their secrets; Benny wants to be a porn star and Jo wants to be with a girl; she’s not gay but she’s been always curious.

Fortunately for Castiel, he remained a winner; in more than one treat.

**

 Friday went by with Castiel being unable to concentrate of any work he had scheduled. When the night came, tired as he was, all he was able to do was lying in bed daydreaming of what will happen the day after. A threesome is something rare, if you come to think of it, people don’t usually go through life asking friends to take part in such an activity. Well, in my opinion they should. But this is not my story so let me go back to the show stars.

When Cas manages to fall asleep the clock has just struck three and the last thought going through Castiel’s is starred by a pair of full lips and the best of the smiles. He hasn’t fallen asleep with a hard on in years; or woken up with a harder one, as a matter of fact.

So on Saturday morning he takes a light breakfast and begins to check his entire wardrobe, he actually literally takes his whole closet out- no pun intended- and going through every single piece of clothing he owns; picking up a grey AC/DC T-shirt, his favorite black khakis and his new electric blue Converse- which everybody says is the same shade of blue as his eyes. And yet, there’s a small item he can’t find among his possessions: a suitable pair of boxer briefs. All his underwear is old, ugly or won’t fit right, so he makes an executive decision; he’s going shopping.

Castiel goes to the Mall and into his favorite shop, he browses the underwear section and the only thing he finds appealing is a pair of black boxer briefs with a bright red hem. That’ll have to do. He buys it.

Dean decides to go for his dark green shirt that makes the green of his eyes pop, and his favorite jeans, torn at the knee level. It takes him like five minutes to pick his whole outfit and he thinks he might be becoming a chick because it took him too long to decide.

Anna went shopping as well. If everything goes as expected then this is gonna be a one-time-only thing, it also means that probably she won’t get laid tonight and will have to settle to touch herself looking at them performing. She can work with that, couldn’t you?

If it doesn’t work the way she hopes, then she’ll end up having a threesome with two gorgeous guys. That merits new lingerie. So she goes shopping and picks up some beautiful and sexy thing; a black sild bra with lace which continues in a sort of a lace apron with little red bows, all along with a black seen through lace thong; thong so small that the back of it seems inexistent. When she gets back home with the shiny shopping bag she selects a loose flowered dress to dress on top.

The afternoon comes and Anna gets everything ready. In the bedroom she lights candles that scents the room very girly. Damn Benny and his ‘dinner-first’ idea, well, probably he’s got a point. If Cas was as bold as Dean they wouldn’t need anything to relax and set the mood, nothing more than a few drinks perhaps. But Castiel is too shy, and for the sake of the plan she cooks a light meal; a meat salad, with blue cheese, lettuce and nuts, all sprinkled with a creamy dressing. Good enough for Dean not to complain about rabbit food and light enough for them not to be so full and heavy to fall asleep in the middle of, well- of ‘it’.

It’s five minutes to seven and, with everything else ready, Anna pours some wine and waits. Castiel is always very punctual so she knows he’s gonna knock any time now.

And here he is.

Anna opens the door to a very nervous Castiel but at least he is there, and that’s a relief. She invites him in and kisses him on the lips, just a peck but just intimate enough to loosen him a bit.

“Hello, Anna” Castiel smiles, dropping the jacket he’s been wearing over his T-shirt on the chair by the door,

“This is weird, I’m not sure I’ll be able to… I mean, I’ll… I’ll try but- I don’t know” He takes a few seconds to run his eyes all over her body, “You look gorgeous, my friend”

“Well, nice of you to notice” she’s being purposely coy, “Here, have some wine. Loosen yourself a little before Dean arrives.” She smiles at the flinch in Cas eyes, she’s so fucking right about these two, “He’s always late, anyway, he’ll probably be here in fifteen minutes” she takes a few sips of her own wine, “So, Castiel, I’d take the chance to ask you what are your limits, is there anything you don’t want to do, like at all? My policy is clear rules- I’ve done my research, you see?”

“I’ve made mine too and that left me more confused and frightened than before”

“Look, Cas, if you feel uncomfortable we can just have dinner and chat. I wouldn’t want you to feel compelled to do something against your will”

“No, don’t worry about that, I’m definitely in. It’s just that- what if Dean doesn’t like me; or what if I do something he or you don’t like?”

“But Cas, there is nothing different than plain sex; well, probably more hands and mouths and will take longer than usual, because there are more people involved but it’s still just us, I promise you’ll be perfect. Now let’s talk about your NO-NOS”

“What? I don’t know”

“Let me help. Will you be okay around him while you both are naked?”

“Yeah, I think so” Cas ponders, and his dick is not twitching at the thought.

“Good, now; what if he touches you” Cas eyebrows lift, “I mean, like touching your back or kiss or, I don’t know, if he… strokes you?”

“Uhg, my back wouldn’t be a problem, or my neck or face; I’m not sure about kissing and I don’t think him touching my dick is…”

“Okay, so, no dick touching on Dean’s behalf. Alright, anything else you don’t like me to do? Like biting, marking or fingering?” Anna tests, she already knows most of Dean’s no-nos, anyway.

“I’ve never tried biting and about fingering… probably not” she’d hang on to the ‘probably’.

“Alright, so all in all, your no’s are dick touching and probably no fingering” She pours some more wine in her glass, “Anything else?”

“No, Anna, I don’t think so” Cas says sipping the last of his wine and handing the glass for Anna to fill it again.

Twenty minutes after Cas arrived the doorbell rings, “Just in time. Be a dear and pour some more wine, Cas” Anna instructs him as she goes to open the door.

“Hi, baby. How are you?” Anna lets Dean in, kissing him while looking straight into Cas’ eyes. The kiss Dean and Anna share is a little longer and more passionate than the one she shared with Castiel.

The show is on.

“Come on, let’s get some wine and talk a little. I’ve talk with Cas already and you’ve got the same no-nos so there’s no need to discuss it any further. I say let’s eat and relax a bit”

“Salad? Really, Anna? I understand this is your fantasy but… salad?” Dean takes his seat anyway.

“Yes, salad, mister no-rabbit-food, but it has more meat than vegetables in it, so stop complaining” Anna is amused.

They eat talking about anything but sex, relaxing and laughing. It feels like any other time they’ve gotten to go out together. Dean and Cas expressively avoid each other’s gaze but from time to time they seem to forget what they’re here for and stare at each other intensively, like they do every time they think no one sees them, making Anna smile to herself.

The mood is light but the elephant is still in the room and getting bigger by the minute, and Dean thinks it actually gets a little pinker, too. With that in mind he attempts to make the first move to get things going or chances are he’s gonna get loony.                                                                                                                                                                                                                                                                                                                                                                                                                                                                              Anna feels the air getting heavier and the reason is the desire the three of them are emanating. She’s into this till the end.

They get up and while Anna and Dean move to the couch, Cas picks up the table and goes to do the dishes. Anna understands he does it out of distress, he’s really nervous and she thinks that letting him do the dishes is gonna help him relax. Castiel can see them start touching on the couch and well, maybe the cutlery is not that clean.

While putting the last plate onto the drying rack he hears the music beginning to play. Beethoven. Anna picked it up because she knows is Cas’ favorite, and also knows Dean is not gonna complain. They both know that, out of the three of them, Cas is the one that needs to relax the most or nothing’s gonna happen.

“Come on Cassie, Hurry up or we’ll start without you” she teases him while he rinses his hands.

He turns to see Dean has lost his shoes and is sat spread, arms across the back of the couch, Anna is standing in front of Dean and motions to invite Cas to sit on the other end of the couch, he does and loses his Converse and his socks, watching with the corner of his eyes how Anna pulls a rope on her waist and the flower dress falls to the floor.

Anna actually hears Dean stops breathing and sees Cas eyes open wide. Of course they’re stunned; she’s gorgeous and gloriously half naked. Who would remain stoic? She smiles, she’s got them exactly where she wants them. She dances, sexy moves that would have made Beethoven blush, and yet, who would blame him?

She makes a turn to show the guys what’s waiting for them, exposing her full attire; she goes sitting on the couch in the middle of the two men. They switch positions to face her and Anna takes Cas hand and puts it over her breast and turns to kiss Dean. For a few seconds, Cas shyly cups her breast but then he moves closer and starts kissing her neck, making her moan.

She starts unbuttoning Dean’s shirt without breaking the kiss; Cas stands up and, still kissing her neck, he takes her up with him and holds her from behind while Dean takes his shirt off, also standing up, joining the kissing on the other side of Anna’s neck.

The men explore her body, front and behind; Cas cups her breasts and Dean strokes her thighs; she whimpers feeling her head spinning. Damn she’s enjoying this way too much, what was the plan again?

Her back feels the loss of the warmth of Castiel’s body when he moves to take his T-shirt off, she takes the chance to guide his hands to remove her bra and then untie the bow lace in the small of her back; leaving the thong as the only piece of clothing left in her.

Dean takes a step back to admire Anna’s body, “Anna, you’re so beautiful” but then his eyes move a bit the left and Boom!, wild Castiel in nothing but black khakis appears in his vision field. Dean’s eyes discovering his friend’s firm and gorgeous body; who would have known. Dean forgets how to breathe.

Cas can feel Dean’s eyes on him but he tries to concentrate on Anna, feeling his knees beginning to buckle all the same. There in front of him there’s an incredibly beautiful man looking at him like he wants to eat him up. Dean deep kisses Anna and Cas murmurs in her ear beautiful words of praise, causing Anna to purr.

Dean finds the show in front of him very erotic so he sits back on the couch to watch. He watches Cas kissing Anna’s shoulder while pinching her nipples and rolling them between his fingers. He’s harder and harder, she feels his dick against her ass and almost drools at the thought that it seems to be pretty thick. Cas locks sight with Dean, sliding his hand through her belly and pulling her harder against himself, letting his hand go further south. Dean unbuttons his jeans and opens his fly, palming his dick softly; Cas could have sworn Dean’s eyes were green, but right now they’re completely dark of desire. Cas continues to work on Anna’s body, worshiping her but his eyes never leave Dean’s actions and he’s harder than ever. Cas’ inhibitions flown away.

Castiel’s hands reach the hem of Anna’s thong, playing with it without moving the fabric. His index moves towards her clit and moves in small circles over the fabric, one hand on her right nipple and another over her clit. She has to scream, the ecstasy overwhelming. She forgets about the plan, about her friends’ eye fucking; the only thing that exists is the touch of Castiel’s hands and lips.

Dean removes his jeans and the tent in his black boxers with a red hem is huge. Anna smiles at the sight; she already knows that Dean is big and tastes amazing; but now Cas is driving her crazy and all she can think of is to taste Cas’ cock, to have them both in her mouth and inside her.

To hell with the plan… for a while.

Dean stands up and takes her left breast in his mouth, just scratching the nipple with his teeth, sucking afterwards; and Anna cries his name. Cas head is a confusion of lust and want, he pushes aside her thong and fingers her with his index while his thumb presses over her clit.

Anna can’t take it any longer, she grabs Dean by the hair and brings him up shoving her tongue into his mouth, kissing him deep and rough, moaning, stealing his breath. When she finds she can no longer breathe she leads Dean back to her breast.

“Bite a little harder” she orders him and he complies. She’s close, the men feel it. Cas feels it in the trembling of her hips, Dean on the beating of her heart and the spasms of her breathing.

Three fingers inside her from behind, Cas moving them in and out, in and out without break, his other hand stroking her clit, sucking the skin on her shoulder blade. Dean grabs her breasts and licks and bites and licks again; and she comes in al low and long cry, almost fainting but Dean is fast and grabs her to prevent her falling on the floor.

They wrap her around with their arms and take her to the bedroom, the candle light playing shadows on the walls; the perfume in the air, coming from candles and bodies alike, intoxicating.

Cas lets Anna in Dean’s arms while finally stripping form his khakis. Dean looks at him and stops breathing altogether, they have the same taste in boxers and, fuck, Cas is gorgeous. Suddenly Dean wants to bend him over the dresser and fuck him until Castiel forgets his own name, and then let Cas bend him and fuck his brains out. And now if Dean doesn’t stop this line of thought he’ll forget about Anna and this is her fantasy. So he reluctantly takes his eyes off Castiel and places her on the bed, stroking her hair waiting for her to come back down from her orgasm.

“Always so considerate” she manages to breathe out, her head clear and still horny as hell. She moves to kiss Dean’s chest, Castiel looking at the scene form the side of the bed.

Anna pushes Dean off the bed, doing the same herself, grabbing both men’s boxers and tugging them down so they step out of their underwear. She was right; Cas is big too, almost as big as Dean and she drools at the thought of it.

She takes their hands and they look at her in confusion; she sits on the edge of the bed and takes them towards her. Oh, now they get it. The two men look at each other and whimper at the feeling of her hand on their dicks. Dean feels a familiar warmth in the tip of his cock and turns to her, copping her face, slightly moving his hips. She takes turns with each dick, sucking one while stroking the other. She eats them whole in turn and Cas can’t help but to moan loudly. The men shut their eyes, lost in sensations but open wide again when they feel she takes both cocks in her mouth at the same time.

Dean thinks he’s dies right there he wouldn’t care less; Cas is dizzy and so horny he could actually explode. They are so horny that none of them notices that their dicks are touching.

Dean watches Cas cock disappearing into Anna’s mouth and feels the heat in his guts announcing the impending orgasm, but she quizzes the base of his dick and stops eating Cas to say, “No, big boy… not yet” and takes Dean’s deep into her throat. She strokes Cas while eating Dean and then she switches again and keeps on going for a while until the men think that she’s probably trying to kill them. She strokes them one more time and turns to the nightstand, taking out a box full of condoms and a bottle of lube.

She’s got this part already planned.

“I want Cas at my back so Dean gets to open me for him; it’s only fair” the sounds coming out of both men are impossible to classify. She does want to drive them mad. Anna goes to the bed and gets on her hands and knees, turns her angelical face to meet Dean’s eyes, “It’s okay, baby”, winking at him smiling at the growling sound Dean makes while leaning on her, “Cas, go and sit, you can watch us from the chair” That breaks the spell Cas has been under, he goes to the chair and looks at Dean work Anna’s rear.

He watches Dean remove her thong, stroke her thighs and touch her clit while opening her cheeks and lick her hole. She purrs, makes little noises and a predatory look lands on Cas. He has to palm his hard cock and licks his lips. Cas sees Dean open the lube and put some on his fingers; without pause, stroking her clit introducing one finger through the rim, making her complain so Dean stops, “No! Don’t stop! You know the drill, baby”

He squeezes her cheeks and gets more lube on his fingers entering her again, this time with more ease. Now she whimpers making little backward moves, fucking herself into his finger. He gets the memo and introduces a second finger, opening her, scissoring her rim; kissing her back, the other hand pressing on the clit, making it pulse and grow. One more finger in and she’s ready.

Dean whispers on her ear, “How do you want him?”

“Ah, yes, on his back” she can barely speak.

Dean looks at Cas as he comes on the bed and lies on his back, his cock bouncing and pulsing, looking delicious. He takes a condom and puts it on, opening his legs to receive her. He lubes himself and waits.

Anna has to be strong and remember her original plan, “Cas, honey, this position is tricky, let Dean help you put your dick in me” Dean almost chocks and looks at Cas, Cas looks back at him, blue eyes gone completely black.

“Go ahead” he says, he’s having the best sex ever and he wants Dean to touch him, Dean licks his full lips and grabs Castiel’s cock with a lubed hand and needs to remind himself what he’s supposed to do with it; the temptation is too strong.

Dean strokes Cas twice, three times, their eyes locked and then guides him inside Anna. He holds Castiel until he’s seated inside her and of course that’s not weird at all; Dean wouldn’t care, though.

Anna cries at the fullness, loving it, holding him down, keeping him still so to get used to him. Dean puts a condom on and fills her pussy in a single thrust, desperate for her heat and her tightness.

She’s full, wholly full and she’s almost there. The two men stay still for a while, expectant, and compliant, giving her time to accommodate to the fullness.

Dean can’t take it any longer, this is the best sex he’s ever had- and he had plenty- and in addition to Anna’s hotness, there’s a pair of eyes at her back looking straight into his soul.

He has to move.

Cas can feel him moving through the veil of her tunnel, he feels him against his own cock, Oh God, he’s gonna come early as a teenager, so he won’t move, but as Anna moves along with Dean she moves on him too.

Dean’s friction makes Anna crazy and it’s enough for all of them. It takes no time to take her to the verge, she can feel it building in slowly; Dean fastens the pace, sliding in feels like stroking Cas dick and it’s amazing, he doesn’t want this to ever stop. With closed eyes, Dean bends to kiss Anna but she moves a bit to the left and he ends up kissing Castiel instead, and it’s shocking to realize none of them tries to avoid it; instead Dean feels Cas hand on the back of his neck deepening the kiss, both of them moving frantically now, almost forgetting their lady friend is between them, until Anna cries all the way to the end of a new orgasm, strong and loud; and they have to break the kiss to allow her to move.

She jumps, taking Dean off of her, sitting on Cas dick and taking Dean’s condom off to suck him hard and steady, moving fast on Cas cock. She feels them close so she encourages them, stroking Dean and moving herself up and down on Cas, she makes them come within a few seconds away and the sounds they both make sounds suspiciously like each other’s names, but she won’t call them on that. She sucks Dean clean and Cas goes to the bathroom to clean himself.

When he comes back to bed he finds Anna hugging Dean’s chest, so he places himself on her back and joins the group hug. Five minutes later both men are asleep. Anna smiles, her work is done and she had her own reward; she lays there happy and sated not ready to move… she manages to do it half an hour later when she slips from in between the men and, fighting the dizziness, she takes a quick shower, gets dressed and leaves to Benny’s. Proud of herself and her work well done and if she enjoyed it beyond the plan nobody cares. She’s giving them the night to sort themselves out.

As soon as Anna moved from the middle of the bed, both Cas and Dean moved towards each other seeking for the lost warmth, unaware in their tired sleep, that Anna is gone.

A few hours later Cas wakes up, tired but satisfied with last night activities. Eyes still closed he feels the warmth against his skin and smiles at the memories of what they’ve done. Anna had been awesome and so had been Dean. Fuck. His dick twitches at the memory of Dean’s lips on him.

Something feels odd, not wrong… just odd. There seems to be more room on the bed and he misses the soft round forms of Anna against him. He opens his eyes and takes a look at the ceiling and onto his left side… Yes, this is still Anna’s apartment. Castiel looks over his shoulder without moving his torso and smiles at the sight of Dean, sound asleep, next to him. He keeps his place on the bed because he waits for Anna to be back from the bathroom or the kitchen, but something’s not right… there’s too much silence… he waits and waits and at a point he realizes that Anna must have left; he checks the clock on the night stand and sees it’s too early, she must have left on purpose. He’s lost in his thoughts when he feels an arm over him, Dean is hugging him from behind, Castiel lets him; he starts caressing Dean’s arm feeling his erection growing and pushing against his ass… he should be shocked or at least a bit worried but he finds it comfortable enough to let himself fantasize about it all. He likes what’s going on in his mind. This is a fantasy weekend so what the hell.

Castiel moves his hips backwards; pushing into Dean’s hard on, he brings Dean’s hand to his lips and sucks his finger while rocking his hips. Dean purrs and opens one eye, tenses and freaks out for a second.

“Is this okay, Dean?” Cas turns to face Dean, concerned that he’s pressing him into something he doesn’t want.

Dean seems to think for a split second, but the memory of Castiel’s lips on his comes back and he relaxes. Dean resumes hugging Cas and coyly says, “Yes, Cas, it is okay. Now stop talking and kiss me”

They kiss for hours, not ready just yet to go any further. Dean explores Cas’ mouth, tracing doodle patterns on his back, bodies aligned, legs entwined, and all too comfortable to let go. All of a sudden Dean remembers they’re still at Anna’s house and startles. Castiel buffs a laugh.

“Relax Dean, she’s not here. I think she left us alone and I think she did it because she knew we would want time alone.”

Dean leans back on the bed, he doesn’t care about the reason she’s gone as long as she’s not around to interrupt them. He cups Cas face, drinking from those blue eyes he’s been dreaming for a long time now; gets closer and pecks Cas lips and trails little soft kisses towards his neck. He kisses him there, all kind of kisses. Raspberry kiss, soft touch of the lips kiss, open mouth kiss, a tiny sucking kiss. Castiel hisses and moans. Dean loves it.

“First time, Cas?” Dean asks without stopping his journey through Cas’ neck.

“Yeah… you are the first guy I kissed, the first guy I’m naked in bed with and the first one that has touched my dick; and the only one I want to do it all again with” Cas whispers back.

Dean murmurs on Cas’ ear, “Me too”.  He resumes the kissing and that leads to exploring each other bodies with hands and mouths. Cas finds that Dean has a spot at the back of his neck where kissing drives him crazy, Dean finds out that Castiel likes to be bitten. At the same time Cas realizes that Dean likes to be grabbed by the hair and takes mental note to use that information when he gets Dean to suck his dick. His dick approves the plan with a twitch. Dean finds out Cas has a spot on his inner tight that makes him scream, and he’s planning to make him scream a lot… he loves his voice.

Exploring leads them to want more.

Cas, the shy guy; the guy who would stare at him but wouldn’t dare to even try a proper chitchat, can have the filthiest mouth and turn into a brave bastard that would make the first move.

“Suck my cock”, Cas orders and a hesitant Dean lifts his gaze from his groin, where he was still licking that sweet spot in his inner tight. It only takes a two seconds thought to make his decision. The moment Dean feels his hair taken into Castiel’s fist he finds nothing else to ponder about. He lets his lover move his head by the hair and, without unlocking their eyes, he kisses Cas’ tip. Castiel tightens his fingers and Dean takes him a little deeper, lost in the sound of the other man’s deep moans. Castiel whines and buffs, unable to stop and not really caring; the warmth of Dean’s mouth, the care the freckled man puts in the task is enough for Castiel to lose his mind. Dean is so focused in moving his head up and down and licking from bottom to top, that he feels he can remain there for ever; his eyes closed, all senses trapping and saving memories of the taste, the texture and the smells. He’s so focused that he’s taken by surprise when Castiel takes him up, cupping his face and kissing him, liking inside his mouth and straddling him.

“I wanna taste you and fuck you and I think it’d be just fare that you fuck me too”, Cas says with such a deep voice that Dean’s hips thrust up almost coming right there.

Dean clears his throat, “Okay, big boy, what you wanna do first?” he teases but soon enough he tries and fails to suppress a gasp when Castiel goes down, hands and knees on the bed and says, “Taste you” just before licking Dean’s shaft.

There’s no expertise in any of them, but they’re eager enough towards each other to do their best. Cas helps his tongue with his hand and strokes Dean a few times before the green eyes shut and his mouth throws a plea, “Stop!” and Castiel panics for a split second thinking that maybe Dean doesn’t want this after all.

“Wait, please. Remember all the things you said you wanted to do… I want them too. I would like you to fuck me.” Castiel looks down at him in awe, “You know how to open me or do you want me to do it myself?”

Castiel sits on his heels, hands on his tighs, and smirks, “Oh I know how to, but I would love to see you doing it”, he takes the lube from the nightstand and throws it to Dean, “Play it for me, Dean”

Fuck, that was hot.

“Cas, you kinky bastard” Dean leans on his back, opens his legs, lubes his fingers and slowly begins to introduce them, one at the time, in his ass.

Castiel feels his mouth water at the sight, his cock complains at the lack of attention, twitches with every finger passing Dean’s rim. “Next time, Dean, because I want to do this a lot of times, I’ll eat you” Dean moans and rocks his hips while he scissors his fingers, “this is not the first time you do this to yourself, isn’t it? You filthy boy!”, Cas reaches for his own dick, stroking slightly and tongue darting out moistening his lips.

Dean flushes red, “No, it’s not. I’ve been fingering myself while stroking my dick… and I closing my eyes to pretend it was you doing it” He bites his lower lip and winks at Castiel.

“Shit. Next time I’ll make you come like that. Now get ready” he crawls on top of Dean and stops when their mouths are aligned.

“I’m ready for you, Cas” Dean takes a condom and puts it on Cas shaft. He’s about to move on his stomach but Castiel stops him. They stare to each other for a moment, green and blue eyes blown black of arousal.

Castiel lifts Dean’s legs and sets the tip of his dick at Dean’s entrance, toying with the rim; Dean takes him by the neck and gets his face towards his own, “Now, Cas… please”, Castiel groans and pushes in, entering with a long, even thrust… he doesn’t stop, he couldn’t… it feels so tight and warm and right. Once he’s settled inside Dean, he makes the ultimate effort to stay still, giving Dean time to adjust to the intrusion. He leans forwards and kisses Dean soft and deep, with Dean’s hands on his back, scratching, caressing; his muscles quivering with the effort to remain unmoving. Dean can feel it.

“Cas, move please” he asks in a whimper; Cas complains and starts a slow ascending pace.

“I wanna see you cum, Dean… Come for me” Cas takes Dean’s dick and starts stroking his dick at unison with his own thrusts, he knows none of them is gonna last long… they’ve waited too long for this. Every time Cas moves, the head passes by that sweet spot inside Dean’s insides and the guy’s brain is all fireworks. With all those hours of foreplay and the years of fantasizing about Castiel, Dean is ready for that sensation that is rapidly growing in his groin. Just a few strokes and thrust later he comes with a scream all over his belly, a scream that sounded like his lover’s name.

Castiel lets Dean’s cock to take him by the hips and thrust into him deeply and stronger, a few moments later he cries his way into his release, filling the condom with his seed, rocking his hips refusing to leave home. He slumps over Dean and drowns him with kisses.

Gone soft, he slips out of Dean making him moan complaining at the loss, “I’ll be right back” he pecks Dean and somehow manages to stand up and goes to the bathroom to retrieve a wet towel to clean himself and Dean as well. They start kissing again, happy and sated as never before. They fall asleep almost immediately, this time it’s Cas turn to be the big spoon.

Hours later Dean awakes to an empty bed and, chest clutched in fear, panics for a moment, then he hears Cas humming somewhere around the department. Smiling to himself, he gets up, puts on the boxers briefs he finds on the floor, takes something from the night stand and follows the sound of his lover’s voice to find him at the kitchen making breakfast dressed only in his matching boxers.

“Hey, sunshine!” Dean watches Castiel from the kitchen door, admiring the broad back of the man of his obsessions, “I think you are wearing my briefs, these ones are too tight for me” he says, approaching him from behind and hugging him by the waist and taking a second to hide what he had taken from the bedroom behind the cookie jar.

Castiel turns around smiling widely and kisses him tenderly, “Morning gorgeous, I think you’re right, we can exchange underwear later.”

“Is this weird for you?” Dean asks suddenly concerned at the other man turning back to cook so quickly.

“Not at all. It should be, though, but somehow it isn’t, Dean. Nothing feels weird between us, does it?” Castiel looks at Dean over his shoulder, wrinkling his nose, “I’ve been into you since we met but I didn’t want to assume it. How about you, Dean; is it weird to you? What am I to you?...” Castiel completely turns around now, facing Dean with a questioning look, worried look even, “Am I a one night stand? Because if that’s what I am to you…. I mean, it’s okay by me but I would very much like to continue being one until Anna returns, if you know what I mean” he crooks his eyebrows and winks.

Dean smiles worrying his lower lip and looking at the floor for a split second, “No, Cas. I’ve always care about you; you’d never be a one night stand plan for me. And yet yes, it is weird” Now Castiel flinches a bit, suddenly hurt, but Dean lifts his hand to stop Cas from continue overthinking, “It is weird because it feels natural, even normal… Hell, Cas, it feels great, man! Like home, you know?” he takes a look at the clock on the wall, “And talking about home maybe we should…”

“She called” Cas cuts him, “She said that we have the house to ourselves till noon and that we should expect her to arrive with Benny for lunch.” Castiel shrugs a bit, lowers his voice an octave and offers, “It’s 8AM… you could have breakfast… and me and then we could clean the place a bit”

Dean discovers that Castiel is a fine cook and in the middle of pancakes, eggs with a side of bacon breakfast he asks him to marry him and without thinking Cas says ‘Yes’. There’s exactly a two second silence and then they burst in laughter.

They clean up the table, Dean washing, Castiel drying. The last mug in its place and as Cas is turning away from the counter he finds Dean’s arms pulling him in a tight wrap and his mouth pressed against his.

It’s time for Dean to fulfill his own fantasy. The dresser is out of the question because it has too many things on top, so the counter is a good second option. He cups Castiel’s face with one hand and with the other clasped around his waist, keeping him close, their bodies aligned and searching for friction. Dean feels Cas’ hands on his back, stroking, scratching… going down to cup his ass cheeks, squeezing. That’s too much, Dean turns Castiel around and bends him on the counter; arms around Cas’ chest, keeping him in position to kiss his shoulder blades and trace a path of sucking kisses along his spine, making Castiel push his ass against Dean. Castiel takes one of Dean’s hands and sucks his fingers. Both men are groaning and moving as if there were not enough hands and mouths involved, as if they’d need more and more.

Dean takes the lube from behind the jar and drops to his knees taking down Castiel’s boxer; he parts his lover’s ass, biting the cheeks and darting his tongue out to lick the rim. He smiles when he feels Castiel’s knees almost buckling, his legs trembling. He carefully opens him while lubing his fingers and lovingly begins to work him, “Have you ever play with yourself like this?” Dean asks, finding him incredibly tight.

“Nuh uh, you’re the first one there… Oh, God!” Cas whines as Dean hits his prostate.

“Relax, Cas, I got you, my love” Dean reaches Cas’ dick with his other hand and squeezes at the base, “It feels odd and it’ll probably hurt at first but I promise it’s awesome” Dean continues the reassurance.

“Dean, stop talking and fuck me already, please!”

Dean doesn’t have to be told twice, within a hair’s breadth he’s putting the condom on and presses the head against the rim, pushing in carefully; as the head goes in Castiel realizes that Dean was right, it hurts but at the same time it feels right and all kinds of awesome so he tries not to show he’s hurt, still he cannot help but to hiss.

“God, sorry, Cas” Dean stops cold, “You want me to stop?”

“NO! No, please… I want this… I saw you enjoying it last night, I want that too… I need you, Dean”

Dean sighs, relieved and willing to oblige. He continues thrusting evenly until he bottoms out. Remains still, kissing Cas’ back, “Cas you’re so tight… God, I love it; you’re so fucking tight I’m not gonna last… you’re perfect… tell me when I can move…” he licks the spine line.

“I swear that if you don’t move now, Dean…” Cas doesn’t have to finish the sentence, Dean groans and begins to move slowly, almost as if not at all. Castiel whines, Dean rocks a little faster with every moan and whine from Cas but he’s still being way too carefully slowly, “Fuck, Dean… c’mon, I won’t break!”

That’s all Dean needs, he fastens the pace and with every thrust he goes further out and then further in, hitting the prostate every time. Faster and harder until the counter complains and they startle a bit but then Dean says, “Fuck it, I can buy Anna a new one”, he continues to fuck into Cas, feeling his orgasm building, his thrusts becoming erratic and desperate. He moves his hand on Castiel’s cock at the same rhythm as his thrusts.

“Shit, Dean, I’m close… so fucking close… shitshitshit…” Cas rumbles.

“Come for me, Cas… come for me, Babe” Dean encourages him, feeling his own orgasm closer with every stroke.

They both come with each other’s name on the lips. Dean collapses on top of Cas, kissing his neck. “I love you, man, I want to do this for the rest of my life so, what’ya say… when’s the wedding?” Dean jokes.

Cas looks over his shoulder, eyes glowing with a shade of satisfied sky blue, “A year from today.” A moan complaining when Dean pulls out of him, “That was amazing” he turns around to face Dean and kisses him deeply, clinging on his shoulders and gripping his hair. He looks straight into those green eyes he’s been loving since he can remember and sighs, “’Say we clean the place and have a shower… let’s go green and share the shower”

They clean up the kitchen, change the sheets, put the bedclothes into the washer and while they wait for the washing cycle to finish they end up entangled in a 69 on the couch. They take their joint shower, unable to stop themselves from playing the athletes and have a stand up sex session on the shower. They clean each other, kissing and caressing; afterwards they towel admiring each other’s bodies. They put their own boxers on and, as Cas is taking his trousers from the bed, Dean takes him, wraps his arms around his back, strokes his hair and pecks him on the tip of the nose.

“I think I’m falling for you” he whispers.

Cas smiles sweetly, “I love you, Dean. All these years telling myself that you were just a friend, I was just lying to myself. I wasn’t joking when I said ‘A year from today’”

Dean’s face glows with joy, “I wasn’t joking when I asked. I love you too”

They hug and kiss for what it seems hours and when Dean checks his watch he realizes it’s 11.50AM and they rush to finish dressing, barely on time before the front door is opened and Anna and Benny enter the apartment.

“Is my apartment clean?” Anna shouts from the living room. Smiling when she sees them coming from the bedroom.

“Spotless” Cas answers, kissing Anna on the cheek. Dean does the same and they both shake hands with Benny.

“I wouldn’t use the couch, bed, shower or counter for a while, though” Dean flushes red, “Buy we cleaned every surface and even put the sheets in the washer”

“AHHHHHHHH TMI” Anna laughs… “No, seriously… I want more mental images… spill!!”

“Yeah, you dogs! I want to know more…” Benny makes himself comfortable to hear the whole story, “NOW… who played who? Who likes what? Come on, people… throw us a bone! It’s the first time two of my straight friends come out of the closet at the same time… with each other and I even got to help!”

“Help? How did you help?” Cas says with a grin.

“Oh, man! You’re not that stupid. You must have realized at a point that this was a squirm, right?” Ben buffs.

“Well, last night between kissing Cas and the owner of the place ditching us in the middle of the night… well, yeah, we got it… it was all some sort of Let’s-Get-Dean-and-Cas-Together plot” Dean laughs.

“Good for you… now spill” Benny leans forward, ready for the story.

Dean’s never been known for deflecting a challenge, “We took turns and we both loved it. I was on my back on the bed; I bent him over the counter. We did a stand up in the shower and we 69 on the couch” Dean teases him making Benny cheer with his hands on the air.

“Oh, and put this date next year on your calendars. He proposed and I said yes. He was serious and so was I… save the date, you’ll be our best men” Castiel says holding Dean’s hand.

Dean won’t give them a minute to process all the information, their shocked faces are too precious, “Oh and Anna, we need to talk, baby. I know you’re in love with me,” Anna laughs, “yeah, yeah… anyway, I need to tell you I’m in love with somebody else and that it’s your entire fault. Last night was an awesome way to end my straight sex life. You were fucking awesome, girl. Best.Threesome. Ever.” Dean finishes with a serious look in his face. Anna punches him on the shoulder.

Benny and Cas laughs out loud, “Oh, yes, Anna, you were amazing, really utterly amazing and yes, baby, that was an unforgettable way to say our straight lives good bye.” Cas says, hugging Dean from behind and kissing his neck.

“Hey! Don’t eat in front of the poor!” Benny complains, “My boyfriend is out of town for another three days” he pouts.

“Blow me” Dean answers, hugging Cas tighter; both men looking at each other lovingly, they kiss again and Dean’s middle finger may have lift in Benny’s direction by mistake… or not.

“Nah, you both were a delicatessen when you were straight… now you’re only two gay guys shagging each other” Benny jokes, leaving the couch to hug Anna, “Great job, girl! ‘M so proud of you. You turned them gay and now they won’t keep the PDA to themselves” he says kissing Anna’s temple.

The doorbell rings.

“Alright, love birds; lunch has arrived” Anna says opening the door to the pizza guy.

**

Exactly 365 days later, happy days with eventual fights with its subsequent make up sex; Cas and Dean take their vows in front of all their family and friends. Their best man, Anna, is standing next to them. She’s the responsible of this union, after all.

The next 365 days have been intense, happy days and eventual fights, jealousy scenes and hand in hand walks through the park. All too normal.

The day arrives; Anna, the person who did it all to get them together, proudly stands on the altar as best man. The happy couple walks the aisle arm in arm, as equals. They get to the altar and turn around for a moment to face their families and friends, they look at each other for a moment, and they sigh and smile watery smiles, full of joy and love. They turn to face the Minister as he begins the ceremony.

“We are gathered here to witness the union of Dean Winchester and Castiel Novak in Sacred Matrimony…”

 

 

**Author's Note:**

> You can leave kudos and comments because we looooooooooooove them... you can also read our other works here [Naniquena](http://archiveofourown.org/users/naniquena/) and here [Fridarules](http://archiveofourown.org/users/fridarules)


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